


A Deal's a Deal

by 3R1D4N_4MPOR4



Category: RWBY
Genre: Age Difference, Bathroom Control, Cervix Penetration, Daddy Kink, Dirty Talk, Excessive Pee, F/M, Face Slapping, Face-Fucking, Multiple Endings, Probably not anatomically correct, Public Humiliation, Public Nudity, Roman is kind of an asshole, Roman just straight up decks her at one point, Rough Oral Sex, Rough Sex, Vibrators, Watersports, Wetting
Language: English
Status: Completed
Published: 2018-08-31
Updated: 2018-08-31
Packaged: 2019-07-04 23:49:31
Rating: Explicit
Warnings: Underage
Chapters: 6
Words: 4,333
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15851940
Author URL: https://archiveofourown.org/users/3R1D4N_4MPOR4/pseuds/3R1D4N_4MPOR4
Summary: Ruby needs credits to fix Crescent Rose, so she goes to the richest guy she knows.  Unfortunately, he's not just gonna give it to her.  (Somewhat inspired by "Ore ga Kanojo o *su Wake – Episode 3")





	1. The Deal

**Author's Note:**

> This is my first time writing something with chapters, so feedback is appreciated!

Ruby needs credits to fix Crescent Rose, so she goes to the richest guy she knows. Unfortunately, he's not just gonna give it to her.

Roman Torchwick is a man with standards and knows that everything comes at a price, so when his favorite little huntress showed up at his hideout with a totally not worried expression and a proposition, he began digging in his mental vault for the worst thing he could ask for in return. The amount of credits she needed was insane, so he should get something just as insane from her. He could have her as his slave for the day, renounce her team and Beacon to be his sidekick, hell he could just kill her right there and not even have to worry about her anymore. But then his mind started to get a bit perverse. His idea started out lewd and it just kept getting worse as he piled on more and more ideas into one big idea that was gonna make Ruby regret ever coming to him for money. He presented his deal. If Ruby could go on a day long walk with him, he'd buy her whatever she wanted the next day. Sounds easy enough, right? But there's a catch. She would have to do it with a vibrating dildo pushed into her as far as it will go. She can't take it out, she can't masturbate, and worst of all, she can't go to the bathroom at all. She has to hold it all day. If she can make it, he'll take her on the shopping trip of a lifetime. If not, she suffers a lifetime of embarrassment. However, Ruby had confidence in her abilities. She agrees to his deal and they meet back at the same place the next day to get started.


	2. The Date

**Summary for the Chapter:**

> The plan is put into action. Let's see how long Ruby can hold out

At roughly 8am, Ruby is given the rundown of their trip. They start here and make their way through Beacon with Ruby showing him the sights, then through the port and into the shopping district. He'll pay for lunch when they get downtown whether she fails or not. Once done there, they travel to a park that's really pretty this time of year. After a sufficient amount of time, they backtrack through the entire route to make it back to Roman's place as the sun's going down. An entire day planned out. And if anyone asks why they're together, Ruby has to explain that she's in the process of rehabilitating him, and showing him around to see all the lives he could help by being a good guy is the first thing on the agenda. With the route set, Roman supplies the toys of Ruby's demise. A bright pink ribbed dildo with a remote control that's going to stay in Roman's pocket. He turns away so she can pull down her underwear and push the toy inside of her as far as she can. She's only had sex once, maybe twice, so she's already bright in the face and fuzzy in the head. It gets worse when Roman clicks the button on his remote that turns the vibration on. It's on the lowest setting, but it's enough to make Ruby moan and mewl and almost buckle at the knees. After a minute to adjust, Ruby practices walking until she can at least not look like a toddler in a teenager's body, which is their que to leave and get started on the long day ahead of them.  


Thankfully the walk through Beacon is uneventful. Most of the students are either still sleeping or in class and the ones who are out and about are upperclassmen who didn't know who Ruby even was. Once they leave the grounds, Roman reaches into his jacket pocket and turns the vibrator up one setting, which he will do again once they get past their next location. It takes Ruby a minute to get adjusted, but she pulls through. At about 10:30am, they reach the pier. Seagulls overhead caw and chirp as ocean waves slap against the docks. It's a beautiful sight, really. Thankfully Ruby used the bathroom before she came to Roman so the sound of water didn't trigger her need to go again, much to Roman's dismay. They get through just fine, and Roman turns the vibrations up again, causing Ruby to have to brace herself against a nearby wall. She rubs her legs together uncomfortably, but Roman lands a swift smack of his cane against her ass to remind her that she can't do that. The smack unfortunately causes Ruby to cum immediately, almost on command. She throws her hand over her mouth to muffle her scream as a clear liquid dribbles down her leg. Luckily, she packed plenty of napkins in one of her pouches, so once she recovers, she pulls a few out and wipes up any visible fluids. Roman tries to tell her that she lost already, but she reminds him that he said she couldn't pee, but he didn't say she couldn't cum. He nods and lets her finish before they continue on.  


They make it into the shopping district by 11:20am and begin window shopping. More people are staring at them as time goes on either because of how red faced and wobbly Ruby is or because she's with a wanted criminal. Nobody asks though, they just go about their day and make a note of it to tell their family members about who they saw in the shopping district when they get home. Rubes and Torchy make their way past many stores, observing the different wares with touristic intentions, making notes in their heads of where to go tomorrow if Ruby wins. It doesn't take long for 12pm to roll around, so they take a break to get lunch while they're downtown. Ruby suggest A Simple Wok and Torchwick agrees, figuring he'd trust the person who eats there regularly.  


They both sit down on a stool and order noodles, chatting while they wait. Torchwick, in his ever generous ways, turns off the vibrator while they eat to give Ruby a break. She's thankful, but he adds a stipulation. She has to drink all of the biggest cup size the noodle place has. After her earlier orgasm, she did need a drink, so she reluctantly agrees. They both get their noodles and Ruby chugs a huge cup of tea, almost 20oz of liquid. She can't finish her noodles because her stomach is so full of tea, so Roman carries her leftovers for her because, as he put it, he's "a generous man".  


1:20pm rolls around and they've finally made it to the park. It is very well populated this time of day, and Ruby is growing concerned. The tea went through her way faster than she expected, filling her bladder to the point that it hurt. Due to that and the increased level of vibrations that came with leaving downtown, Rubes became more sluggish and afraid to move. She felt so open and vulnerable, feeling that the slightest touch or bump would cause her to spill.


	3. The Dirty Talk

**Summary for the Chapter:**

> Roman turns the tides in his favor

"Well Red, you've made if farther than I thought you would. I'd usher a congratulations, but the day isn't over yet." Roman smiles tauntingly at her, leaning close with his weight on his cane. "Did you at least enjoy lunch? I know I did!"  


"Yeah, it was alright." Ruby's voice is drained of personality, sounding slow and dull, fearing that even talking could set her off.  


"I bet the tea was delicious, wasn't it?" He shoots her a cheeky look, but she just stares at him like she's a prisoner of war and he's her warden that likes to dangle food in front of her only to snatch it away at the last second. "Aw Red, why are you so down? Cheer up, we're at a park! Plenty of fresh air!" His voice lowers as he leans close to her ear. "And plenty of people to see you fall." His voice sends shivers down her spine, but she remains strong. She made it this far, she can make it home. He waits for her to say something, but after a minute of silence, he shrugs and motions for her to follow. "Well whatever, at least we can swing together!" He smiles as he walks on the sidewalk with his girl at his side. He notices she's been gradually slowing down, and at this point, it's just making him mad that she's taking so long. So Roman in his infinite wisdom decides to make it worse for her. He slows down so she can keep up with him, but as they walk, Roman leans down to whisper in her ear some more. "Are you already gonna pop? It's only been a few hours, and you, the silver-eyed warrior, are already about to piss yourself after having just one drink. Tsk tsk, what are these people gonna think when they see the Ruby Rose pee all over her panties and boots? And what could be worse? Not only did you wet yourself in public, but you were walking around all day with a vibrator constantly humming in your cunt. You're just a teenager and people will already think you're a filthy slut. A slut that would do anything for money. You'd be the laughing stock of Beacon. Hell, you'd probably be kicked out. All because you came to the wrong person for money." He finishes his monologue with a wicked smirk as Ruby is on the brink of tears. What's worse is as she was distracted by his words, he had turned her vibrator to max and lined her up at just the right angle for a jogger to bump into her shoulder and knock her flat on her ass. And that was it.  


Ruby cried out loud when she hit the pavement, her legs flew up just enough for the jet stream of piss that shot out of her vagina to fly a good distance before soaking the ground.  


" **HEY EVERYONE LOOK, RUBY ROSE IS PISSING HER PANTIES!!** " Roman wasted no time pointing to Ruby and announcing the sight to everyone, all eyes turning her. Some people laughed, others averted their eyes, and a few got their scrolls out for pictures. All Ruby could do was lay there and begin to cry, unsuccessfully trying to stop the powerful stream. Roman didn't want to waste this opportunity, reaching down to yank her panties off and pull out the neon pink vibrator so her piss could travel further with no obstructions. " **And what's this!?** " He holds the soaking wet vibrator in the air for everyone to see. " **Ms. Ruby Rose had a vibrator shoved up inside her the entire time! In public!** He announced loud enough for the world to hear. More people were taking pictures and videos, and one girl was even fingering herself under her skirt to the sight of it all. Ruby's scroll is blowing up with notifications of being tagged in thousands of social media posts and concerning texts from friends asking what's going on. 

Finally after about 5 straight minutes, her river runs dry and she's able to stand. Her face is beet red, her eyes are puffy, and her cheeks are stained with tears. With all her might, she rears back and punches Roman as hard as she can before running back home as fast as she can with her semblance, leaving the park in a wake of rose petals. 


	4. The Divide

**Summary for the Chapter:**

> Ruby is understandably sad. She was humiliated in front of the entire world! There's really nothing she can do now. Or is there?

It's been weeks since the incident. General Ironwood created a kill code for every piece of technology in the world and has wiped every single trace of the incident from everything, and even afterwards, he fixed Crescent Rose himself so Ruby wouldn't need to pay for new parts and even offered her a private job at Atlas if she was that desparate for money. She politely declined, saying she doesn't want to leave her room. No one has been able to drag her out of there. She barely eats, her grades are plummeting, and team RWBY is lacking without it's leader. Without her it's just WBY, which just sounds like ooby. It's funny if you say it out loud cause it's one letter away from booby but that's not the point. The point is Ruby is scared and alone and practically at death's door.

**Notes for the Chapter:**

> This chapter is short because it leads to a fork in the road!
> 
> If you want a good ending, go to the next chapter!  
> If you want a bad ending, go to chapter 6 instead!


	5. The Daftermath

**Summary for the Chapter:**

> Happy ending with tons of teammates!
> 
> (I couldn't find a synonym for aftermath that started with a "d" so)

Fortunately for her, Death's Door just got kicked in by a big ass boot. The rest of team WBY, team JNPR, half of team SSSN, and even half of team STRQ come barging in, flicking on the lights, throwing open the curtains, and all surrounding Ruby in a ring of friendship and support. Ruby wipes the death from her eyes and looks around, suddenly crowded by her friends and family. She hides her face in shame at the sight of her father, but he just sits down next to her on her bed and places a gentle, loving hand on her back.  


"Hey kiddo, I know you've had a rough few weeks, but you can't let it stop you from achieving your dream." He says softly as if she were a baby again and he's tucking her in for the night.  


"Th-Thanks, but-" Ruby tries to speak, but she's interrupted by Yang.  


"But nothing! Just because you had an accident outside doesn't mean you can't become the world's greatest huntress! You gotta put your past behind you Rubes." Yang offers her own words of encouragement.  


"Yeah, besides, plenty of us have done embarrassing things in public." Jaune chimes in, trying to at least cheer her up. "Just a few days ago, Neptune tripped and fell face first into a puddle of water, then freaked out and ran into a glass door!"  


"Dude, you said you wouldn't tell anybody!" Neptune whines from wherever her is in the crowded room.  


"Sorry, I'm tryna cheer her up!"  


"Hey, let's not forget that Sun peed his pants not too long ago!" Nora snickered and poked Sun in the shoulder.  


"Yes, but Sun finds that to be sexually pleasing." Ren informs Nora, who, in shock, turns to Sun. Sun shrugs and nods, agreeing that he's into it.  


"ANYWAY," Qrow speaks up, putting the topic back on track, "don't even worry about the fact that it was for money, I've done worse for less."  


"What did you do?" Pyrrha can't help but ask.  


"Trust me kiddo, you're too young to know." He pats her head affectionately.  


"Granted, what happened was disgusting, and I'm going to avoid touching you until after you've had at least five showers, you're still our teammate, and we still love you!" Weiss tries to offer her best.  


"What do you say, Ruby. Are you ready to make WBY RWBY again?" Blake offers a hand in friendship. It takes Ruby to accept it, but she nods and grabs on, letting Blake help her to her feet as everyone else cheers.  


"Now come on, let's get some food in you, you're probably starving!" Yang beams at her newly empowered younger sister.  


"Yeah! But let's not get any tea, okay?" Ruby finally smiles as everyone started heading out to get some well deserved dinner.

**Notes for the Chapter:**

> This is the good end! If you want a darker ending, go to the next chapter


	6. The Dirty Deeds

**Summary for the Chapter:**

> Ruby had a taste of a different life, and now she wants more

As Ruby lays in her bed, her thoughts swirl in her brain like a confusing cocktail of emotions. It took some time to process, and she doesn't want to admit it, but the sheer thrill of the entire experience was intoxicating. Being watched by all those eyes as she did the unthinkable in broad daylight, it was sickeningly exciting. She's already starting to arouse herself just thinking of doing it again. She wants to, she has to. She springs up from her bed and stares out the window, making one final decision. If she does this, there's no going back. It doesn't take long for her to decide. With a hoodie, pants, a mask, and a bag of her belongings, she pops open the window and, using a rope that she had lying around, she lowers herself to the ground and runs as fast as she can. She runs to Roman.  


When she arrives on his doorstep, she's sweaty and out of breath, but she has a somewhat lopsided grin. After a few knocks at the door, The door opens up, and there's Roman, in all of his disgusting glory.  
"Well well well, what do we have here?" He asks, already knowing the answer just by the symbol on her bag. "Red, what brings you to my humble abode at this hour?" Ruby removes the mask, and Roman can immediately tell what she wants by the darkness in her eyes. "I have a feeling I already know the answer to that. Why don't you come in." He moves so she can step into the inconspicuous home. It was pretty nice, despite the fact that it's just a hideout. Ruby sets her bag down and pulls off her hood, shaking her messy hair out. "So I guess I should ask. Is this an overnight situation? Or is that a permanent bag?"  


"It can be whatever you want, just use me like you wanted to before.." She was holding herself back from jumping on him then and there.  


"Well, if it's fun you want.. Put on your usualy outfit. The frilly red and black one. Cape, boots, everything. But don't put on panties or leggings." His tone shifts from snarky to serious, commanding her with a firm tone. He turns around so she can change, wanting to keep the surprise of her body for later. After about 10 minutes, she tells him she's done. He spins back around and looks her over. She's got her usual outfit on. Perfect. "Alright Red, follow me." He grabs his cane from beside the door and leads her through the hideout and down some stairs into a concrete basement with a dingey drain in the floor, a shower head with knobs on the far back wall, and a dresser on an elevated platform near the door so it wouldn't get wet from the shower. Once inside, Roman locks the door at the top of the stairs and makes his way back down, opening the top drawer of the dresser and dropping the keys into it. He reaches past the key and picks up a pair of handcuffs before closing the drawer, now turning to Ruby. "Gimme your wrist."  


"Yes sir." She smiles at him, and he smiles back, liking the sound of that. When she offers her wrist, he puts one cuff around it, then leads her to the opposide corner of the room where halfway up the wall, a pipe comes out of the wall, then goes back in, making a semi circle. He pushes her down, making her fall on her ass again, then with unnecessary strength, he grabs her wrists and pulls the empty cuff through the pipe and chains Ruby's other wrist to it, making it to where her arms are stuck in the air. She tugs a bit, but she doesn't try to free herself. Roman returns to the dresser and retrieves a small bottle full of a strange purple liquid and a ball gag. He puts the neck of the small bottle between his teeth as he kneels down to situate the gag into Ruby's mouth. After all the preparation is done, he stands back up, removes the bottle from his mouth, twists the cap off, and downs the entire thing with a satisfying 'ahh' afterwards. He tosses the bottle behind him and it clinks very loudly upon hitting the floor.  


"Well my darling little Red, I've been watching to do this since I met you." He unbuttons and unzips his pants, pupping his already stiff dick out of his boxers. He strokes it a bit, seeming to coax it to do as he wants, and sure enough, a hard stream of pis ejects itself from his dick, aiming straight for Ruby's face. Within seconds, her face is soaked. He aims a little higher to get it in her hair, then lower to get her chest. "Hey, spread your legs so I can see your pussy." She nods and complies, shifting her legs so her vagina is in sight. She's soaked down there too, but not by him. He only smirks and readys his deep, sultry voice. "Look at you, you're fucking pathetic. Your cunt is wet as fuck just from me pissing on your face. You're a disgusting whore. And this time it's actually true. You came to me, you wanted this, didn't you. You wanted me to piss all over your favorite frilly little dress, huh? You're a sick fuck, you know that? I bet you have a daddy kink, don't you. I wouldn't put it past you, you disgusting slut. Well guess what, Daddy just drank a potion of liquid control. He could piss on his little princess all night." Ruby's cunt trembled at the thought. She hadn't thought of whether or not she actually had a Daddy kink or not, but she's loving it so far.  


He stops his stream for a moment so he can get down on his knees and straddle her, removing the gag but keeping her mouth open with his hand. "Does Daddy's little Piss Princess want a drink?" He asks in the most condescending way he can.  
"Yes Daddy!" She replies a little too enthusiastically. Roman laughs and shoves his thick cock down her throat, starting his stream again, now pissing directly into her stomach. But that's not enough for him. He grabs her by her hair and starts forcing himself in and out of her, face fucking her with no concern of her well being.  


"Do you like that? Huh? Do you like it when Daddy uses his cock to shut you up?" She tries to nod, but his grip is too strong. After a few minutes, he pulls out and rubs his cock on her face, still letting out a steady stream all over her head. "Are you gonna be a good little girl? Gonna let Daddy do whatever he wants to you?"  


"Yes Daddy..." Ruby replies, almost as if she's in a trance. He stops his stream again, repositioning himself to get another look at her vag.  


"You're such a dirty slut, you're dripping on the floor. You're hungry for Daddy's cock aren't you?" Without warning, he presses two fingers into her, feeling how much she wants him. "Tell me what you want princess, you're a college girl, use your big girl words."  


"I want Daddy's cock..." She started.  


"What do you want Daddy's cock to do? Be more specific!" He slaps her hard across the face, leaving a print.  


"I want Daddy to fuck me with his cock! Fuck me and fill me up with his pee and cum!" She whined, pulling on her cuffs, desperate to touch him.  


"Good girl..." He gets into one last position, propping her hips up in his lap as he slides his shaft through her slit. Her eyes roll back at the sensation, then screw shut as he positions and pushes himself into her. He stretches her out father than she's ever been, hitting her cervix once 3/4 of his cock got in. He starts pumping in and out of her rapidly, not giving her time to adjust. She screams in pain and pleasure as his bell end bashes against her wall. As he's fucking her, he starts peeing again and looks down to admire his work. Streams of piss and lady cum squirt out of her cunt as he pounds it mercilessly. After a good few minutes, he stops, then holds her down firmly as he pushes past her wall, penetrating her cirvex directly and pissing in it, filling it up to max capacity. He takes his sweet time pulling out, admiring just how much pee her body could hold. "Come on baby, stand up for Daddy." He stands up and helps her to her feet. A little bit more drips out of her, but overall, her cervix is holding tight. "Shake your hips for Daddy." He commands. She wiggles her hips, but her cervix still holds. She can feel it move inside of her though. It's heavy and it feels weird. "Do you feel that, Princess? That's all Daddy's pee stored inside of you." After a moment of letting her marvel at her body's ability, he gives a swift punch to her stomach, pushing her cervix to let go of it all. Ruby stumbled, caught off guard by his action, but she's too blissed out to care. Plus her semblance absorbed most of it anyway. After she's empty, Roman gives her a pat on the ass before picking her up and slamming her against the wall, pumping his cock into her again, determined to finish what he started. He does a few slow, deep thrusts before switching to quick, shallow ones, then goes back and forth between the two for a while before he bites his lip and cums pinside of her, finally finishing. For a while, they stay in that position, red faced and panting, until Roman's cock finally empties itself and softens, sliding out of her with the rest of his cum. "How was that, baby?"  


"That was... Amazing..." Ruby can barely talk, and there's no way in hell she's gonna be able to walk that off, so Roman helps her out of her cuffs and brings her over to the showerhead. He tells her to strip while he gets the water going and strips himself. As he's helping her clean herself off, he gets hard again and they go for round two for another half an hour. But after that they're done. They shower, they get clean, and he carries her bridal style to his room so they can sleep togrther. Tomorrow is gonna be training day for Ruby, though. If she's gonna live with him, he's gotta teach her how to drink, swear, steal, and lie.

**Notes for the Chapter:**

> This is the darker ending. If you want a happier ending, go back to chapter 5!


End file.
